Eszopiclone

Base Information

• Chemical Name: Eszopiclone
• CAS No.: 138729-47-2
• Molecular Formula: C17H17ClN6O3
• Molecular Weight: 388.813
• Hs Code.: 2933790002
• European Community (EC) Number: 620-471-1
• UNII: UZX80K71OE
• DSSTox Substance ID: DTXSID8046086
• Nikkaji Number: J573.434G
• Wikipedia: Eszopiclone
• Wikidata: Q413184
• NCI Thesaurus Code: C65545
• RXCUI: 461016
• Pharos Ligand ID: UFYLF5P3HGBB
• Metabolomics Workbench ID: 42763
• ChEMBL ID: CHEMBL1522
• Mol file: 138729-47-2.mol

Synonyms:1-Piperazinecarboxylicacid, 4-methyl-,6-(5-chloro-2-pyridinyl)-6,7-dihydro-7-oxo-5H-pyrrolo[3,4-b]pyrazin-5-yl ester,(S)-;(+)-Zopiclone;(S)-Zopiclone;Estorra;Lunesta;

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Eszopiclone

Chemical Property:

• Appearance/Colour: White or slightly yellowish powder
• Vapor Pressure: 1.78E-13mmHg at 25°C
• Melting Point: 202-204 °C
• Refractive Index: 1.688
• Boiling Point: 580.7 °C at 760 mmHg
• PKA: 6.70±0.10(Predicted)
• Flash Point: 305 °C
• PSA: 91.76000
• Density: 1.54 g/cm³
• LogP: 1.50880
• Storage Temp.: -20°C Freezer
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 388.1050661
• Heavy Atom Count: 27
• Complexity: 573

Purity/Quality:

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-62
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Sedatives and Hypnotics
• Canonical SMILES: CN1CCN(CC1)C(=O)OC2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
• Isomeric SMILES: CN1CCN(CC1)C(=O)O[C@H]2C3=NC=CN=C3C(=O)N2C4=NC=C(C=C4)Cl
• Recent ClinicalTrials: Effectiveness of Combining Behavioral and Pharmacologic Therapy for Complex Insomnia in Veterans With PTSD
• Recent EU Clinical Trials: A randomised, double-blind, double-dummy, placebo-controlled, 3-way crossover study to evaluate potential next-day residual effects of a single evening dose of 3mg eszopiclone and 7.5mg zopiclone in healthy adult subjects.
• Recent NIPH Clinical Trials: A pilot study for the efficacy of the non-benzodiazepine hypnotic or orexin receptor antagonist on insomnia in major depressive patients unresponsive to benzodiazepine hypnotic treatment: a randomized open-label trial.
• Description: Approved by the FDA in December 2004, Eszopiclone is a non-benzodiazepine drug with hypnotic and sedative activity which is effective for the treatment of insomnia characterized by difficulty falling asleep, difficulty maintaining sleep or awakening frequently during the night, waking up too early, an inability to fall back to sleep and awakening in the morning not feeling refreshed. Eszopiclone belongs to cyclopyrrolone and dextrorotatory stereoisomer of zopiclone, which was the first non-benzodiazepine approved for insomnia in over 20 years. However, Eszopiclone is a controlled pharmaceuticals. Long-term intake of this substance or any other sedative drug probably induces drug dependence. Patients may experience withdrawal symptoms if the drug is stopped abruptly. Eszopiclone is a non-benzodiazepine hypnotic agent indicated for the treatment of insomnia to induce sleep and for sleep maintenance. It has similar pharmacokinetic and pharmacodynamic parameters as the previously marketed non-benzodiazepine hypnotics zolpidem and zaleplon. However, unlike its predecessors, eszopiclone is not restricted to short-term treatment of insomnia. Clinical studies of up to 6 months of use show that patients do not develop tolerance to its effect. Eszopiclone is the (S)-enantiomer of zopiclone, which has been marketed as the racemic mixture in Europe for almost 20 years. These agents belong to the cyclopyrrolone class of drugs that act as agonists at the type A GABA receptor. Eszopiclone has approximately 50-fold higher binding affinity than its antipode (R)-zopiclone for GABA-A receptor (IC50=21 and 1130 nM, respectively). In addition, the two enantiomers exhibit significant differences in their pharmacokinetic parameters and in vivo efficacy. In healthy volunteers, eszopiclone has 2-fold higher Cmax and 2-fold greater elimination half-life than the (R)-enantiomer.The two most frequent adverse events associated with eszopiclone treatment are unpleasant taste and headache. Other less frequent side effects include somnolence, dry mouth, and nausea.
• Uses: Eszopiclone is the active stereoizomer of Zopiclone and belongs to the class of drug known as cyclopyrrones. It is a nonbenzodiazepine hypnotic agent used as a treatment for insomnia. This is a controlled substance (depressant) in the US but not in Canada.

Technology Process of Eszopiclone

There total 24 articles about Eszopiclone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(S)-zopiclone N-acetyl-L-aspartate (1107971-15-2) → eszopiclone (138729-47-2)

Guidance literature:

With potassium carbonate; In dichloromethane; water; at 20 ℃; pH=10; Product distribution / selectivity;

Reference yield: 94.0%

(S)-zopiclone N-acetyl-D-aspartate (1107971-05-0) → eszopiclone (138729-47-2)

Guidance literature:

With potassium carbonate; In water; at 20 ℃; for 2h; Product distribution / selectivity;

Reference yield: 91.7%

zopiclon (43200-80-2) → eszopiclone (138729-47-2)

Guidance literature:

zopiclon; With D-Malic acid; In methanol; acetone; at 10 - 56 ℃; for 8.5h;

With potassium carbonate; In water; for 1h; Solvent; Temperature; Reagent/catalyst;

upstream raw materials:

1-methyl-piperazine

(S)-(+)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

6-(5-chloropyridin-2-yl)-7-hydroxy-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

(+/-)-7-(2-chloromethyloxycarbonyloxy)-6-(5-chloropyridin-2-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyrazin-5-one

Downstream raw materials:

(7S)-6-(5-chloro-2-pyridyl)-6,7-dihydro-7-hydroxy-5H-pyrrolo[3,4-b]pyrazin-5-one

zopiclon

C₁₇H₁₇ClN₆O₄

(-)-Zopiclone

Refernces

• 1、 -. "Method for synthesizing eszopiclone". . . Retrieved 2018/04/02.
• 2、 Zaazaa, Hala E.,Salama, Nahla N.,Abd El Halim, Lobna M.,Salem, Maissa Y.,Abd El Fattah, Laila E.. "Strategy Approach for Direct Enantioseparation of Hyoscyamine Sulfate and Zopiclone on a Chiral αl-Acid Glycoprotein Column and Determination of Their Eutomers: Thermodynamic Study of Complexation". . p. 49 - 57. Retrieved 2016/02/20.